My website is www.chetson.com and I am trying to create a layout like this site: http://www.kurtzandblum.com/, namely that the left sidebar is flush with the nav bar, and then there's a picture to the right and then content and the right sidebar just underneath the picture.

Struggling to do this as it seems you can't have a column within a column?

Add a two column section. Size the left to the width you want the sidebar, and the right to the rest of the content. Enter the sidebar in the left and on the right enter media box for your image. Then add in your iboxes and the other sidebar section into the right area, these will then display once under the other. Using the section width options shrink the sidebar section and the iboxes section so they fit into the same space. For example the whole section would be twelve, so set the iboxes to width 8 and sidebar to width 4, you'll see the sidebar moves up to fill the space next to the iboxes.

Tried this previously, but the problem is that I have multiple widgets I'm trying to stack on the right side, and this solution only allows me to choose one thing to have in the right "column." Is there any way to have what is essentially a size bar on the right side with multiple widgets that is under the picture?

I made the progress you suggested in my sandbox site, which is www.chetson.net.

@dchetson You need to create more sidebars with 'Sidebar Manager Light'. To the new sidebar add as many or few widgets, as you would with your primary sidebar . Where @James B† mentions adding a sidebar, you are, in fact, adding a widgetized section that will hold your new sidebar.